E/Z photoisomerization of 3-amino-3-phenylprop-2-enenitriles

Abstract

The E/Z photoisomerization of 3-phenyl-3-(N-substituted amino)-and 3-phenyl-3-(N,N-disubstituted amino)-prop-2-enenitriles was investigated by means of u.v. and ¹³C n.m.r. spectroscopy. Informative results on the mechanism of the reaction produced by direct irradiation of 3-anilino-3-phenylprop-2-enenitrile were obtained from the different effects of quenchers and heavy atoms. Neither the heavy atoms nor the quenchers had any effect on the direct photoisomerization, which involves only the singlet state, by-passing the triplet state.